Friends: The 10 Worst Bosses On The Show, Ranked

The NBC sitcom Friends continues to shine bright and endure because of its relatability. Its 6 characters take fans (especially 20-somethings) through their real-life struggles concerning family, work, and relationships. On the surface, they strike as pulled together, but on a closer look, this ragtag bunch of misfits had their problems.

Speaking of work-life, there was a time when the gang, sitting on the orange couch at Central Perk, in the middle of a workday assumed their bosses disliked them. On other occasions, their bosses were at fault too. It’s easy to wonder who these bosses were and why they disliked the gang so much.

10 Mr. Costellic

In season 1’s “The One With the Stoned Guy” Mr. Costellic (not seen on-screen) asked to see Chandler in his office to tell him he was being promoted to data processing supervisor. Now, ordinarily, being promoted to a higher position should have been a happy thing, but Chandler quit because his stint at the company was supposed to be a temporary thing. To him, taking this promotion meant he’d be making peace with the fact that he was going to be in data processing forever.

Now, Chandler had made it quite clear to Mr. Costellic that he wouldn’t work a job that was making him miserable, but the latter called him over and over again, offered him more money, and finally, the chan-chan man caved. So to summarize, despite Chandler saying he needed a job that he actually cared about, Mr. Costellic went ahead and rehired him. If that isn’t unethical, what is?

9 Chandler Bing

Working under Mr. Costellic had to have its impact on Chandler. As soon as he took the job as the data processing manager, he actually did work overtime (something that he feared) and sat in his office until 12 0’clock at night working about the weekly estimated net usage systems or the WENUS.

The big promotion came with its perks, such as having a huge office with a terrific view and a lot of authority over his juniors. Chandler flirted with an employee named Nina Bookbinder and retained her despite having clear-cut orders to lay her off. When Mr. Douglas caught them together, Chandler spun ridiculous stories to convince him that he’d actually fired her, when in fact, he hadn’t.

8 Dr. Donald Ledbetter

Other than the fact that Dr. Donald Ledbetter had no faith in the brilliant employee, Ross, and refused to sympathize with him in his difficult time, he also stole his sandwich. While yes, Ross was going through a temporary difficult phase, with his second marriage crumbling, and his expulsion, but he was a man who the museum had sent all the way to China in the past.

Ross’s research papers were getting published, he’d tried to break the workplace segregation and he was passionate about his job as well. Besides, There’s absolutely no excuse for Dr. Donald riffling through the office fridge and stealing Ross’s turkey Thanksgiving sandwich.

7 Kim Clozzi

Rachel worked under Kim Clozzi at the Ralph Lauren Corporation and she was a difficult boss. In Kim’s first appearance on season 5’s “The One Where Rachel Smokes,” it became immediately clear that she was a boss Rachel couldn’t disagree with.

Kim was particularly fond of Rachel’s colleague, Nancy, and the two of them made their decisions without her every time they took a smoking break. Rachel was excluded from all the decision-making, and it was neither fair to her, nor to the corporation they worked for.

6 Mr. Kaplan Jr.

What’s with Rachel Green and bad bosses, after all? Mr. Kaplan Jr. was definitely not the friendliest boss on Friends. On Rachel’s first day at Fortunata Fashions, he impolitely ordered her to make the coffee strong for Mr. Kaplan Sr. He also embarrassed her by revealing personal information that should have been kept private.

But most of all, the cruel joke that Kaplan Jr. played on Rachel was the final nail in the coffin. First, he raised her hopes up by telling her there was something worthy of her potential awaiting her, and as it was seen, he ordered her to organize a closet full of coat hangers “ASAP.” Rachel just had to get out of there.

5 The Inappropriate Interviewer

In season 2’s “The One with the Prom Video” Monica interviews for a chef job with a restaurant manager who could have been easily charged for workplace harassment. As she walks into the kitchen with his man, he asks her to make a salad.

Nothing odd or unusual about that, except as Monica proceeds to audition, the manager asks her to narrate the salad-making process. After a host of inappropriate questions, Monica storms out of there. The manager’s blatant questions take a toll on her and it takes her 5 showers to get the interview off of her.

4 Aaron

Ah yes, the World War I movie director who wouldn’t let Joey go because as long as the inebriated actor, Richard Crosby, was conscious and present on set, nothing else mattered. Despite Joey letting him know he was officiating his best friend’s wedding, Aaron ordered him to stay until the end.

While it’s understandable the filming couldn’t have stopped just for Joey, just a cursory look at the lead, Richard Crosby, would have been enough to call it off. Aaron was obviously rushing through the scenes and doing a disservice to his professions to those working under him.

3 Mr. Leon Rastatter

Monica worked briefly for Mr. Leon Rastatter in season 2, creating Thanksgiving-themed recipes from “Mocklate.” In all fairness, hiring a professional chef right before Thanksgiving was the best (and a creative strategy) to market this newly manufactured synthetic substitute of chocolate, there was the “slight problem” of the FDA approval, though.

Turns out, Mocklate was wasn’t declared safe for consumption by the FDA, and Mr. Rastatter feared whether Monica had consumed a lot. Mr. Rastatter’s vision to make Thanksgiving the Mocklate holiday remained unfulfilled. In the end, Monica met with him again, only to be introduced to another unsafe, and synthetic pistachio substitute called Fishtachios.

2 Joanna

Joanna was an executive and Rachel’s superior at Bloomingdale’s who made her first appearance in season 3’s “The One With the Dollhouse.” Though she liked Chandler and dated him briefly, he described her as “a big, dull dud” but couldn’t muster enough courage to break up with her.

Since Joanna failed to set boundaries by separating her work and personal life (she would order Rachel around at Chandler’s, lock Chandler up in her office), Rachel was insistent Chandler quit toying with her and end the relationship. Joanna was also dismissive of her junior, Sophie, and liked to pick on her, relentlessly. She neither behaved professionally at work nor was she respectful to her superiors.

1 Doug

What can be said of a boss who behaves uncivilly at their colleagues’ engagement party, and likes to be excessively indulged? Doug liked to say Chandler’s last name boisterously, unaware of how loud he was every time he said the name – Bing. It was expected of Chandler to laugh at Doug’s unfunny jokes at all times and coddle him thereby proving he was a self-absorbed and conceited fellow.

In “The One With Ross’s Step Forward” Doug proudly mentioned he was battling multiple lawsuits on account of inappropriate behavior and so far was successfully “knocking them (the lawsuits) out of the park.”

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